Furyl vinyl ketone and homologues



Patented Apr. 7, 1942 UNITED: STATE .i 2,275,638 FUaYL KETONE AND HOMOLOGUES Carl E. Barnes, Worcester, Mass., assign'or, by mesne assignments, to E. I. du Pont de Nemonrs &' Company, Wilmington, Del., a corporation of Delaware No Original application December 6,

1938, Serial No. 244,219. Divided and this applicatlon December 11, 1939, Serial No. 308,645

10 Claims.

This invention relates to monomeric and polymeric vinyl ketones and to methods of making the same.

Synthetic resins are made by polymerization calcium carbonate or other suitable alkaline agent capable of neutralizing any; acid formed and preventing decomposition of the final product thereby. Similarly, furyl ethyl ketone may of various compounds containing the unsaturated be treated with formaldehyde with subsequent group dehydration to form furyl isopropenyl ketone (furyl methyl vinyl ketone) The reactions may I k I p be expressed by the following equation (R being hydrogen, alkyl, halogen etc.) in which ll K2001 (I? the are considered to rearrange them elve .C4HzO-C-CH:+CH2O 0 CIHiOC-C.HICH:OH to form a linear chain havingthe group a CH 0C-CH:CH;OBTCiHiOCCH=CH| "R 1 as a repeating unit. These linear compounds ggjg gz zg g gzz g gg gg 'ggf ggi gzg have the properties of fusibility and "solubility.

v ketone. These ketones may also be prepared by As set forth in my copending application Serial No. 240 529 filed November 15 1938 vinyl methyl "eating the mm alkyl with f ketone and isopropenyl methyl ketone contain a :33; 'g iifi 335 33 3 gig gazmfi fig polymerizable unsaturated methylene group reaction is thought to be as follows, capable of polymerization by a rearrangement of the bonds in such a way as to form a linear chain H having the group CAHIOCCHl+CHi0+( HI) HiC1 o=c-cn; cinio -cnrcmmcnomcwmo R This last compound loses dimethyl ammonium as a repeating unit in which R is H or chloride with the formation of furyl vinyl In accordance with this invention, I have 0 kewne: made furyl vinyl ketone and furyl isopropenyl (E ketone and I have found that these will poly- H merize and produce resins that may be used as CHFC o shaped articles or as bonds for granular material, etc. The compounds contain both a polya merizable vinyl group and the furan group con- Furyl vmyl ketone boils at 85 whne taining double bonds conjugated with this group. mryl 150N096! ketonihmfls at 92 (M10 This conjugation is believed to activate the vinyl These Substances as g if f group in such a way that its tendency toward stantiany transparent liquids w 0 p0 me e polymerization is greatly enhanced 40 under standard polymerizing conditions to form The primary object of this invention is to transparent solid bodies which are'hnear polyvide monomeric and polymeric substances cum mers having a high refractive index. These sub- 1 1 stances may be used with base substances formfuryl vinyl ketone and fury isopmpeny ing copolymers therewith. Suitable cross link- Another object is to provide monomeric and mg agents may be used' such as a compound with polymeric substances for use in the manufacture two or more polymerizable unsaturated math f various articles including optical bodies ylene groups in the same molecule. During the molded articles and bodies of bonded granular Polymerizatlon the gmwmg chains incorporate t i l, Further obje ts 111 be apparent in molecules of both substances forming a three the following disclosure. dimensional structure. The number of linkages Furyl vinyl ketone may be made by treating between the linear chains vary with the amount iuryl methyl ketone with formaldehyde in the of the cross linking agent used, hence compounds presence of potassium carbonate or other suitof various degrees of hardness and solubility able alkaline material, and thereafter .dehydratmay be produced by changing the proportions.

ing the product with iodine in the presence of Suitable substances that may be copolymerized Furyl vinyl ketone and refraction, and these substances may therefore be used to modify the refractive index of other polymerizable substances and copolymers containing the same.

It is to be understood that while I have at tempted to explain this invention in the light of the present accepted theory, the claims are not to be construed as dependent upon any particular theory relative to the formation 'of the substances herein claimed. Hence, the above description is to be interpreted as illustrating the general principles of the invention and my preferred manner of making the desired compounds and not as being limitations upon the case except as set forth in the claims appended hereto.

This case is a division of my copending ap plication Serial No. 244,219 filed December 6, 1938.

I claim 1. A composition of matter comprising a compound selected from the group consisting of furyl vinyl ketone and furyl isopropenyl ketone.

2. A monomeric substance selected from the group consisting of furyl vinyl ketone and furyl isopropenyl ketone. v

3.. A polymeric substance derived by the polymerization of a material containing a substance selected from the group consisting of furyl vinyl ketone and furyl isoproperryl ketone.

4'. A polymeric substance selected frbhijthe amuse w group consisting of furyl vinyl ketone and furyl isopropenyl ketone.

5. Furyl vinyl ketone.

6. Furyl isopropenyl ketone. v

7. The method of making a compound from the group consisting of furyl-vinyl ketone and furyl i'sopropenyl ketone, comprising the steps of treating a ketone from the group consisting of .furyl methyl ketone and furyl ethyl ketone, with formaldehyde in the presence of an alkaline material and thereafter dehydrating the alcohol thus formed. 8. .{Ihe method of making a compound from the'group vconsisting of furyl vinyl'ketone and furyl isopropenyl ketone, comprising the steps of treating a ketone from the group consisting of '"furyl'methyl ketone and furyl ethyl ketone, with formaldehydeln the presence of an alkaline materlal and thereafter dehydrating the alcohol thus formed with iodine in the presence of an alkaline substance capable of neutralizing any acid thus formed.

9.Method of making a compound from the group consisting of furyl vinyl ketone and furyl isopropenyl ketone, comprising the steps of treating a'keto'ne' from the group consisting of furyl methyl ketone and furyl ethyl ketone, with formaldehyde in the presence of an alkaline carbonate and thereafter dehydrating the alcohol thus formed. a A l0. Method of making ,a' compound from the group onsistinglof-furyl vinyl ketone and furyl isopropenyl ketone, comprising the steps of treating a ketone from the group consisting of furyl methyl ketone and furyl ethyl ketone, with formaldehyde in the presence of analkaline carbonate and thereafter ,dehydrating th alcohol thus formed with iodine in thepresence of calcium carbonate. r

CARL E. BARNES.

Certificate of Correction Patent No. 2,278,638 April 7, 1942. CARL E. BARNES It is hereby certified that error appears inthe printed specification of the above.

numbered patent requiring correction as follows: Page 1, second column, lines 34 and 35, for that portion of the formula reading and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case inuthe Patent Oflice.

Signed and sealed this 9th day of June, A. D. 1942.

[SEAL] HENRY VAN ARSDALE Acting Commissioner of l atents. 

